DE1954189C3 - Process for the preparation of ethyl 4-hydroxy-6,7-diisobutoxy-3-quinolinecarboxylate - Google Patents
Process for the preparation of ethyl 4-hydroxy-6,7-diisobutoxy-3-quinolinecarboxylateInfo
- Publication number
- DE1954189C3 DE1954189C3 DE19691954189 DE1954189A DE1954189C3 DE 1954189 C3 DE1954189 C3 DE 1954189C3 DE 19691954189 DE19691954189 DE 19691954189 DE 1954189 A DE1954189 A DE 1954189A DE 1954189 C3 DE1954189 C3 DE 1954189C3
- Authority
- DE
- Germany
- Prior art keywords
- ethyl
- diisobutoxy
- hydroxy
- quinolinecarboxylate
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- LVVXOXRUTDAKFE-UHFFFAOYSA-N ethyl 6,7-bis(2-methylpropoxy)-4-oxo-1H-quinoline-3-carboxylate Chemical compound CC(C)COC1=C(OCC(C)C)C=C2C(=O)C(C(=O)OCC)=CNC2=C1 LVVXOXRUTDAKFE-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- DLYUQMMRRRQYAE-UHFFFAOYSA-N Phosphorus pentoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- -1 diethyl 3,4-diisobutoxyanilinomethylene Chemical group 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 125000004492 methyl ester group Chemical group 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JNSVDAVXLICPQY-UHFFFAOYSA-N 2,2-dimethylbicyclo[4.1.0]hepta-3,5-diene Chemical group CC1(C)C=CC=C2CC12 JNSVDAVXLICPQY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003224 coccidiostatic agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 231100000078 corrosive Toxicity 0.000 description 1
- 231100001010 corrosive Toxicity 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L propanedioate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Description
dadurch gekennzeichnet, daß man den aus Phosphorpentoxid und Methanol oder Äthanol entstehenden Methyl- oder Äthylester der Phosphorsäure mit Diäthyl-3,4-diisobutoxyaniiinomethylenmalonat der Formelcharacterized in that one consists of phosphorus pentoxide and methanol or ethanol resulting methyl or ethyl ester of phosphoric acid with diethyl 3,4-diisobutoxyaniiinomethylenmalonat the formula
C1H, O OCC 1 H, O OC
iso-Bu — Oiso-Bu - O
iso-Bu—Oiso-Bu-O
in Xylol erwärmt.heated in xylene.
C-COOCH,C-COOCH,
N-CH HN-CH H
Die Erfindung betrifft ein Verfahren zur Herstellung von Äthyl-4-hydroxy-6,7-diisobutoxy-3-chinolincarboxylat, das ein wertvolles Coccidiostatikum ist.The invention relates to a process for the preparation of ethyl 4-hydroxy-6,7-diisobutoxy-3-quinoline carboxylate, which is a valuable coccidiostat.
Nach dem Stand der Technik ist eine Anzahl von Verfahren bekannt, die z. B. entsprechend den US-Patentschriften 32 67 106 und 33 97 208 von dem Diäthyl-3,4-diisobutoxyanilinomethylenmanolat ausgehen. Die-In the prior art a number of methods are known, e.g. B. in accordance with the US patents 32 67 106 and 33 97 208 of the diethyl 3,4-diisobutoxyanilinomethylene manolate go out. The-
ses Ausgangsmaterial ist, vom wirtschaftlichen Standpunkt aus gesehen, eine teure Substanz. Es ist daher wünschenswert, diese Substanz auf eine möglichst einfache und wirkungsvolle Weise mit hoher Ausbeute in das Endprodukt umzuwandeln.This raw material is an expensive substance from an economic point of view. It is therefore desirable to obtain this substance in the simplest and most effective manner possible with high yield to convert into the final product.
Es hat sich nun gezeigt, daß Ester der Phosphorsäure, die auf die von Mukaiyama und T s u j i a k i (in Bill. Chem. Soc. Japan, 34: 99-101, 1961) beschriebene Weise hergestellt wurden, sehr geeignet sind, um Diäthyl-3,4-diisobutoxyanilinomeihylenmaionat in das Äthyl^-hydroxy-e^-diisobutoxy-S-chinolincarboxylat umzuwandeln. Bei Verwendung dieser Ester ist es nicht nötig, bei verhältnismäßig hohen Temperaturen zu arbeiten und mit Glas ausgekleidete Gerste zu verwenden. Es entstehen kein korrodierender Chlorwasserstoff und keine gemischten Salze. Hierdurch wird ein einfaches Verfahren erreicht, wobei die Ausbeute und die Qualität des Endproduktes nicht vermindert, sondern verbessert wird.It has now been shown that esters of phosphoric acid, which are based on those of Mukaiyama and T s u j i a k i (in Bill. Chem. Soc. Japan, 34: 99-101, 1961) are very suitable to Diethyl 3,4-diisobutoxyanilinomeihylenmaionat into the ethyl ^ -hydroxy-e ^ -diisobutoxy-S-quinolinecarboxylate to convert. When using these esters, it is not necessary to use at relatively high temperatures work and use glass-lined barley. No corrosive hydrogen chloride is produced and no mixed salts. This achieves a simple process, with the yield and the quality of the end product is not reduced, but improved.
Das erfindungsgemäße Verfahren ist dadurch gekennzeichnet, daß man den aus Phosphorpentoxid und Methanol oder Äthanol entstehenden Methyl- oder Äthylester der Phosphorsäure mit Diäthyl-3,4-diisobutoxyanilinomethylenmalonat in Xylol erwärmt.The inventive method is characterized in that one of phosphorus pentoxide and Methanol or ethanol formed methyl or ethyl ester of phosphoric acid with diethyl 3,4-diisobutoxyanilinomethylene malonate heated in xylene.
Die Erfindung soll in den folgenden Beispielen näher erläutert werden.The invention is to be explained in more detail in the following examples.
Zu 366 g Phosphorpentoxid und 640 ml Xylol wurden 209 ml Äthanol unter Kühlen im Eisbad mit einer Geschwindigkeit zugegeben, daß die Temperatur immer unter 1000C blieb. Das Gemisch wurde auf 70°C abgekühlt; dann wurden 407 g (1 Mol) Diäthyl-3,4-diisobutoxyanilinomethylenmalonat zugegeben. Das Reaktionsgemisch wurde anschließend 30 min auf 138 bis 14O0C erhitzt und in 1200 ml Wasser gegossen. Nach 1 stündigem Rühren wurde das Äthyl-4-hydroxy-6,7-diisobutoxy-3-chinolincarboxylat gesammelt und mit Wasser und anschließend mit 200 ml Aceton gewaschen. Ausbeute 330 g, =91,4%; Fp. 278 bis 282° C.To 366 g of phosphorus pentoxide and 640 ml of xylene, 209 ml of ethanol were added under cooling in an ice bath at a rate that the temperature always remained below 100 0 C. The mixture was cooled to 70 ° C; then 407 g (1 mol) of diethyl 3,4-diisobutoxyanilinomethylene malonate were added. The reaction mixture was then heated for 30 minutes at 138 to 14O 0 C and poured into 1200 ml of water. After stirring for 1 hour, the ethyl 4-hydroxy-6,7-diisobutoxy-3-quinoline carboxylate was collected and washed with water and then with 200 ml of acetone. Yield 330 g, = 91.4%; Mp. 278 to 282 ° C.
Beispiel Zwischen- P2O5Example intermediate P2O5
produkt*)product*)
ε gε g
Alkohol mlAlcohol ml
Lösungsmittel Temperatur, Zeit AusbeuteSolvent temperature, time yield
ml %ml%
Reinh. gradReinh. Degree
21
56
56
63
63
63
36621
56
56
63
63
63
366
140-147
30 min
140-148140-147
30 min
140-148
140
1 h140
1 h
140-185
10 min
140-147
15 min
140-145
25 min
138-141
30 min140-185
10 min
140-147
15 minutes
140-145
25 min
138-141
30 min
*) Diäthyl-S^-diisobutoxyanilinomethylenmalonat.*) Diethyl S ^ -diisobutoxyanilinomethylene malonate.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77131068A | 1968-10-28 | 1968-10-28 | |
| US77131068 | 1968-10-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1954189A1 DE1954189A1 (en) | 1970-05-27 |
| DE1954189B2 DE1954189B2 (en) | 1977-05-12 |
| DE1954189C3 true DE1954189C3 (en) | 1977-12-29 |
Family
ID=
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